- Air Conditioner
- Balcony/Terrace
- Bedding/Linens
Villas in Windward Side
Stay in a Villas in Windward Side – Plan Your Next Vacation to Windward Side Today!
Guests
Find the Best Villas for Your Windward Side Trip
Smartours makes it easy to discover stays that match your style, budget, and location.
Why Book Your Trip to Windward Side with Smartours?
Here’s why smart travelers plan travel with Smartours
Smarter Stays
Villas selected for comfort, location and value – giving you the ideal base for your adventures.
Smarter Itineraries
AI-powered trip plans that bundle accommodations, transport, and activities into flexible packages you can tailor to your style and budget.
Smarter Exploration
Self-guided itineraries filled with local insights, hidden gems, and authentic experiences beyond the typical tourist trail.
How to Book Your Stay in Windward Side?
What’s the Smartours booking process?
Our platform connects you to a curated selection of Villas in Windward Side. Once you’ve found your ideal property, you’ll be redirected to our trusted booking partner to complete your reservation securely and with confidence.
Booking Steps
Search Stays
Use Smartours filters to find accommodations that match your style, location preferences, and budget.
View Details
Click on a listing to see photos, amenities, reviews, and pricing.
Book Securely
Follow the link to finalize your reservation directly with our verified booking partner.
Common Trip Amenities in Windward Side?
What amenities can you expect on your Smartours trip?
Our handpicked Villas in Windward Side are chosen for comfort, convenience, and style — often with thoughtful extras to make your trip even more memorable. Here’s what you might look forward to
Indoor Features
- Fully equipped kitchens or kitchenettes
- Comfortable living areas with smart TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-room coffee and tea facilities
- Premium bedding for restful nights
- Modern bathrooms with walk-in showers or soaking tubs
Outdoor Amenities
- Balconies, terraces, or rooftop lounges with scenic views
- Swimming pools, either private or shared
- Outdoor dining spaces with BBQ or grill access
- Gardens or courtyards for relaxing downtime
- On-site parking or easy transport access
- Proximity to key attractions, markets, or nature trails
Seasonal Weather in Windward Side
What’s the weather like in Windward Side throughout the year?
Windward Side’s climate varies by region, but most areas enjoy mild to warm weather year-round. Coastal cities benefit from ocean breezes, while inland areas and the desert see greater temperature swings between day and night.
Frequently Asked Questions
What are the top rated Villa Rentals in Windward Side?
There are a lot of options in Windward Side. If you plan on staying in the Windward Side area, consider making a reservation for a few nights at one of these properties as these have been rated the top Villa Rentals in Windward Side:
- El Momo Cottages
- Saba Arawak Hotel
- Scenery Hotel Saba
- Compass Cottage: Breathtaking Views on Saba, the Caribbean’s “Unspoiled Queen”
- Beautiful Traditional Saba Cottage With all the Modern Amenities
- El Momo Cottages
- Saba Arawak Hotel
- Queen’s hotel, bar & kitchen
- Home a way from home in the Unspoiled queen of the Caribbean.
- Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!
What is the rate per night for renting a villa near Windward Side?
At Smartours, the average rental fee for standard villas in Windward Side is $588 per night. Smartours has a large database of quality villas near Windward Side that are suitable for families, a romantic getaway, or a solo trip with single or multiple bedrooms.
Do you have a villa in Windward Side that allows pets?
Yes, here are the top villas rentals in Windward Side that are pet friendly:
- Spyglass is a Private Villa With 360 View Near Windwardside.
- Modern Luxury Private Villa w Pool and Ocean Views. Walk to Beach. Sleeps 6.
- Saba's FInest Luxury Rental
- Haiku House, an amazing wooden villa situated in a tropical forest
- Compass Cottage: Breathtaking Views on Saba, the Caribbean’s “Unspoiled Queen”
- El Momo Cottages
- El Momo Cottages
- Beautiful Traditional Saba Cottage With all the Modern Amenities
Are there any rental villas in Windward Side that are suitable for families?
Most of our listed villas are suitable for families. The number of rooms varies, and you can check out the complete list of villas in Windward Side to find what works for you.
Do your rental villas in Windward Side have indoor swimming pools?
Based on the 2026 data from our Smartours site, there are more than 7 private swimming pools or villas with indoor pools in or near Windward Side.




